Category Archives: strategy

CIO 101 for Entrepreneurs

This morning I got to share IT infrastructure, business strategy, and business
architecture tips and recommendations with some local current and future entrepreneurs at The Capitol Post in Old Town Alexandria.  Capitol Post is a great organization focused on inspiring Veteran entrepreneurs to find professional clarity and scale those visions.  They offer several great things, including  a cool co-working space right in North Old Town Alexandria, classes, and a startup accelerator program.

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Here are the slides and strategy template I went through with the group this morning, helping entrepreneurs deal with IT.   We talked about:

We talked about how IT for non-technical entrepreneurs can be like personal finance for non-financial people — it’s very important, but it’s hard to motivate yourself to invest the time you need to understand it, make some solid plans, automate it, and then move on to creating value.

It’s been a year since I last taught at Capitol Post (https://mikehking.com/2015/09/11/talking-technology-bunker-labs/), and it’s great to see how much they’ve grown (the office is beautiful and their getting ready for their next cohort to go through the Bunker Labs DC accelerator.

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Organizational Operating System Upgrade?

I’ve started reading Brian Roberton’s book Holacracy, which talks about an organizational
management approach focused around self-organization and protected autonomy.  It’s an interesting attack on the base assumption that we should build companies in the traditional, top-down approach where a CEO directs leaders who direct other leaders, through layers and layers of business leaders.  Holacracy is the first non-traditional approach I’ve seen to business architecture (designing a company) that is cohesive and specific.  Managing teams with a methodology like Agile Scrum is powerful, but Scrum doesn’t scale to an entire organization, without armies of Scrum of Scrum Masters.  Early in the book, Brian lays out this metaphor of a business having its own operating system (including the org chart, business processes, etc.):

…the operating system underpinning an organization is easy to ignore, yet it’s the foundation on which we build our business processes (the “apps” of organization), and it shapes the human culture as well.  Perhaps because of its invisibility, we haven’t seen many robust alternatives or significant improvements to our modern top-down, predict-and-control “CEO is in charge” OS.  When we unconsciously accept that as our only choice, the best we can do is counteract some of its fundamental weaknesses by bolting on new processes or trying to improve organization-wide culture.  But just as many of our current software applications wouldn’t run well on MS_DOS, the new processes, techniques, or cultural changes we might try to adopt simply won’t run well on an operating system built around an older paradigm.

Brian describes an entire methodology, like some of the prescriptive ceremonies and roles you see in Agile Scrum; which I’m still wrapping my head around.  The core tenets of independent, autonomous roles seems incredibly powerful, because it seems to make companies much more scalable.  And it reminds me of the core factors that Daniel Pink identified in Drive as what employees wants in their job:

  1. Autonomy: People want to have control over their work
  2. Mastery: People want to get better at what they do
  3. Purpose: People want to be part of something that is bigger than they are

Holacracy’s concepts explained in 107 seconds: https://www.youtube.com/watch?v=MUHfVoQUj54

How to Pick IT Systems for your Small Business

If you’re the CIO, Director of Technology, IT Person, or Only Person (Solopreneur) at your organization, here are 5 areas of questions areas to consider when determining if a specific IT system or process would align with your small company’s needs:

  1. Alignment:  Does this system align with your business model (how you do business) and your current infrastructure?
  2. Lock In:  Would this system lock you (Vendor lock-in) into this vendor or system long-term?  Could you export your data and move to another system as you grow?
  3. Investment-worthy:  Is this system worth the investment of money and time (your time, your employees’ time, your customers’ time?
  4. Get Traction:  Would this system get traction with your employees and/or customers?  Does it align with how you do business, or would you spend your time forcing people to use it?
  5. No Huge Risks:  Are there any significant risks (red flags, deal-breakers) that should drive you away from this system? (e.g. cyber security, loss or productivity, removes future options you want)

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Shameless plug:  If you’re interested in learning more about setting up the technology for your company, or future startup, check out this free class I’m teaching next week (Thursday, Sept 10, 2015), sponsored by Capitol Post, in Old Town Alexandria:  Technology 101 for Entrepreneurs (How to Choose to the Best Systems for your Business).

How does a CTO Spend Time?

I’ve recently realized that I’ve been drawing a similar pie graph several times recently, explaining how I spend my time as a Chief Technology Officer (CTO) at a small business.  I thought I’d share for those interested in how I spend my time juggling the demands of CTO across various company priorities.

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If you’re interested in learning more about small business CTO activities, including technology strategy when you’re too small to have a dedicated CTO, check out this free, upcoming training in Old Town Alexandria, sponsored by Capitol Post, that I’m teaching next month (Sept 2015):  Technology 101 for Entrepreneurs (How to Choose to the Best Systems for your Business).

Super-busy? You’re not a Hero, You’re Investing your Time Poorly

I’ve been working some long days recently, trying to balance some big projects at work. I overworkedlove the excitement and intensity that comes from leading big change, whether it’s setting up a new system or process, or chasing a big opportunity.  But I often need to remind myself that great leaders don’t have to work long hours, over-working themselves into a frenzy of stress and bad decision making.  Great leaders plan, delegate, recruit, mentor, and they build systems to ensure things get done well without having to be directly involved.  Like Michael Gerber teaches in The E-Myth Revisited:

Work on your business, not in your business.

Gerber’s book is focused on a company, but the concept also applied well to people who lead projects or teams.  Stop thinking of yourself as a hero when you’re super-busy with something — instead, think about how you can:

  • Better plan projects
  • Recruit great people to support the project
  • Mentor others to be able to contribute effectively without significant oversight from you,
  • Design systems/processes so others can work within those systems without needing your to guide them throughout in each step of the process

Initial reactions to Lean Startup Machine DC

This weekend I experienced the intensity that was Lean Startup Machine DC (#LSMDC).  I went with without lots of expectations — I haven’t read The Lean Startup book, I haven’t been to any similar events, and I didn’t know anyone who had.  It turned out to be an intense, great experience.  The highlight for me was meeting all kinds of fascinating people thinking about or already doing cool stuff in the DC startup/entrepreneurship scene. My initial reaction to lean, with has some significant overlap with agile, is focused on quickly validating business models through real tests of your assumptions.  Not thought experiments, not talking it over with you buddy; but real, tangible ways to test your assumptions by removing assumptions.  For example, an early idea of the team I was on was:

  • Assumption:  people would share job openings on their social networks if they would get paid for helping getting someone hired
  • Realization:  people are protective of their social status, as part of their online identify, and only want to share opportunities that help a friend and/or are associated with a cool company

Much of the weekend was spent wrapping my head around using tools to validate or invalidate assumptions (using tools like Google Ad Words, Facebook ads, talking to domain experts (finding them using your network and social media), and pitching concepts).  In addition, there was a huge focus on collecting “currency” or tangible validation of your idea, which could include letters of intent from vendors, clicks on ads (see http://www.stephaniehay.com/blog/lean-content/), email addresses on a launch page (see http://launchrock.com), initial payments, etc. The weekend started with people pitching ideas on Friday evening and forming teams and ended with a Sunday afternoon series of presentations of each group, focused on their process, what they learned, and their results.  In between, there were some great local people sharing their expertise in entrepreneurship and lean concepts; as well as a team of mentors around to help guide people through the process. Some highlights included:

  • Peter Corbett talking about iStrategyLabs
  • Discussions with Teague Hopkins about the future of the office of CIO
  • Maksim Tsvetovat discussing how social networks grow
  • Stephanie Hay’s discussions on initial tests instead of getting stuck in talking about ideas
  • Great ideas from Chitra Sivanandam about focusing on pain points (and hearing about some of the super-cool stuff she does)
  • Hearing Brian Sowards’ story of how he used lean to iterate a weak idea into a multi-million dollar valuation